Polyethylene polyamines such as diethylenetriamine, triethylene tetramine, and tetraethylenepentamine as well as amine derivatives of these polyethylene amines are known and have been widely used in the manufacture of lubricating formulations and as epoxy curing agents. The following patents are representative of various polyethylene polyamine:
U.S. Pat. No. 547,591 discloses a process for producing polyethylene polyamines by reacting an ethylene amine with monoethanolamine in the presence of silica-alumina catalyst, preferably one containing an acidic phosphorus cocatalyst. Linear polyethylene polyamine such as diethylene triamine and tetraethylenepentamine are produced. Japanese patent publication SHO 58-140571 discloses a process for producing polyamines by the catalytic reduction of a cyanoethylated N-(2-aminoethyl) piperazine. Other cyanoalkylated amines such as the cyanoalkylated derivatives of polyalkylene polyamines including diethylenetriamine and triethylene tetramine are also suggested.
U.S. Pat. No. 4,137,267 discloses a process for producing alkyl-1,3- diamino propanes by contacting an alkyl amino propionitrile with hydrogen and ammonia in the presence of a hydrogenation catalyst. Typically, a C.sub. 10 to C.sub. 20 primary amine is reacted with acrylonitrile or methacrylonitrile in the presence of hydrogen chloride and then catalytically reduced in the presence of hydrogen and ammonia over a hydrogenation catalyst, e.g., platinum, palladium, rhodium, etc.
U.S. Pat. No. 4,552,862 discloses a method for stabilizing pellets of a hydrogenation catalyst during hydrogenation which typically include the hydrogenation of cyanoethylated ethylene containing polyamines. Typically, the polyamine substrate is the cyanoethylated product resulting by the reaction of acrylonitrile with an amine or polyamine which includes piperazine, ethylenediamine, monoethanolamine, diethylenetriamine, and 3-aminopropanol. The catalytic hydrogenation is carried out in the presence of hydrogen and ammonia to prevent trimolecular coupling to produce secondary amines.